Sign up for POLITICO Magazine's weekly email: The Friday Cover

Get Mitch

Even in good times, his face wears an almost cartoonish expression of alarm—like that of a man who’s just remembered that he left the stove on and is miles from home. Gray, watery eyes bulging out from behind his glasses; thin, bloodless lips pursed into a frown. And yet, for nearly 30 years, both in Kentucky and in Washington, D.C., that dour visage has been the face of a raw, even legendary political power.

Mitch McConnell has never been a beloved politician. Over the course of his career, he has been likened to everything from a warmed-over vanilla milkshake to “a man with the natural charisma of an oyster.” But for the 71-year-old Kentucky senator, the minority leader of the United States Senate, that has long been an asset, not a failing. His glower has usually been enough to dissuade those who consider crossing him. “He doesn’t say anything. He just sits there and stares at you,” says one person who has felt McConnell’s ire. “It’s bone-chilling.” While most politicians desperately want to be liked, McConnell has relished—and cultivated—his reputation as a villain. After all, he achieved his iron-fisted grip on the politics of his home state and his fractious party on Capitol Hill through discipline, cunning and, oftentimes, fear. Which is why, at the moments that have found him happiest—winning elections, blocking bills, denying the sheen of bipartisanship to President Barack Obama—he has radiated not joy but menace. Stepping to the microphones at a Capitol press conference some years ago, he announced with the slightest trace of a smile, “Darth Vader has arrived.”

But these are not good times for McConnell, and, for once, his face seems to capture his mood: Mitch McConnell is worried. He is worried that more people in Kentucky now disapprove than approve of the job he’s doing. He is worried that, in Washington, Democrats and Republicans alike now openly question whether he’s still capable of controlling the GOP caucus he worked so hard to lead. He is worried that his office is being bugged and that his wife is being slandered. Perhaps most of all, he is worried that the established political order he embodies is coming apart all around him—imperiling the Republican Party more each day and robbing him of his last best chance to realize the true goal of his career. “Most politicians dream of being president,” his former chief of staff Billy Piper told me. “McConnell dreams of being majority leader.” But instead of plotting to claim the Senate majority, McConnell finds himself just fighting to stay in office. More than at any other time in his nearly three decades as a senator, he’s worried about the bull’s-eye on his back.

For most of Obama’s presidency, McConnell has been the face of Republican obstructionism—never more so than when, in 2010, he declared, “The single most important thing we want to achieve is for President Obama to be a one-term president.” But this obsession with ending political careers now belongs to the Democrats, who have made McConnell their top target in 2014. “You cannot overstate the enthusiasm for defeating Mitch McConnell,” says the Democratic Senatorial Campaign Committee’s Matt Canter. McConnell himself is well aware of the forces gathering against him. “Every liberal in America, every liberal in America, is out to beat us next year,” McConnell told a group of Kentucky supporters in August. Democrats do not disagree with that assessment; they anticipate spending $50 million, or more, to unseat him and have recruited an appealing young challenger.

VIDEO: McConnell vows to make Obama a "one-term president.”

But there are Republicans who want his scalp too. It is a great irony that even though the obstruction-minded McConnell has vexed the Obama administration more than almost any other Republican has these past five years, he has also been the Democrats’ most productive negotiating partner—cutting last-minute, not-so-grand bargains to raise the debt ceiling in 2011, avert the fiscal cliff early this year and, just last month, reopen the federal government and avoid a default. “Does anyone down there know how to make a deal?” McConnell asked when he called Vice President Joe Biden hours before the fiscal-cliff deadline. For such cooperation, some conservatives have branded him a sellout, and worse. “The senator should be retired,” says Matt Hoskins of the Senate Conservatives Fund, which has already spent hundreds of thousands of dollars on anti-McConnell TV ads. And for the first time in his six Senate campaigns, McConnell has drawn a serious primary opponent—a Louisville multi-millionaire named Matt Bevin, who has given Tea Partiers the opportunity to make McConnell their top target in 2014 too.

This two-front assault has boxed McConnell into a corner at the most inopportune moment. The midterm elections of 2014, with their combination of open seats and vulnerable Democratic incumbents, had offered him a chance to finally realize his ambition of seizing the Senate majority leader’s office—which, even if it no longer has quite the stature it did when Lyndon Johnson occupied it, would still afford McConnell the most powerful perch of his long political career. In recent years, he had eagerly recruited Republican candidates and plotted their courses to victory—putting his granular knowledge of turnout patterns and media markets at their disposal. But before he could fully execute these grand plans, members of his own party in Congress began acting in ways that made winning back the Senate less possible for the GOP: derailing immigration reform, obsessing over Obamacare, shutting down the government. Suddenly, McConnell, the man no one dared cross, was essentially powerless to stop the hard-liners because of his own political predicament. Never loved, he was now no longer feared.

His personal quandary is very much sign and symptom of a larger political upheaval, as an increasingly ugly civil war has embroiled the Republican Party, pitting its conservative establishment against its even more conservative Tea Party insurgency. For the moment, the Tea Party is winning. In recent years, it has ousted Republican senators McConnell called friends and peers, veterans such as Indiana’s Richard Lugar and Utah’s Bob Bennett—rock-ribbed conservatives both, but neither afraid of sitting and talking with the Democrats. Lugar’s primary defeat at the Tea Party’s hands last year even appeared to bring the famously disciplined McConnell to the brink of tears on the Senate floor: “You’re a treasure to the Senate and a model of the public servant,” an emotional McConnell said. “We’re sorry to see you go, and I’m sorry to lose your wise counsel.”

Now the insurgents, in taking on McConnell, are challenging the very idea of leadership itself. And they have shown how weak those leaders are. Once known for their ability to instill top-down, lockstep unity, the mandarins of the GOP no longer determine—much less dictate—the direction of their party. The tools they relied on for a generation to keep order in the ranks are either gone (legislated out of existence by Republicans themselves, in the case of congressional earmarks) or have been rendered obsolete: Who needs to toe the line in order to get campaign contributions from Wall Street when a new generation of outside conservative groups, such as the Heritage Action Fund and the Club for Growth, now more than make up the difference for candidates who hew to their agendas?

A “big problem in Washington is there are no followers,” Trent Lott, the retired Republican senator from Mississippi who once had McConnell’s job as party leader, told me. “It used to be you could disagree and debate, but when leadership made the call, you had to follow your leadership. … But not anymore,” he continued. “Institutional power is a lot weaker.” That’s why, on most days this fall, McConnell’s dour, worried face seemed to sum up the plight of the entire Republican establishment.